You’re Not A Loser
Request for @prettysourabbie Hey beautiful!!! I was wondering if I could request a Dean Winchester x plus size reader where she super awkward and while playing truth or dare she admits awkwardly that she never kissed anyone, and after words dean gives her, her first kiss?
Warnings- Benny’s a bit of a dick, self esteem issues
You were laying in your bedroom watching your favorite show, (yfs) and a soft knock came at your door. “Come in.” You say softly.
Dean poked his head in with a smile. “Hey sweetheart. What are you doing?”
“Just watching tv.”
He hummed and looked at the screen, “Again?” He chuckles playfully and it makes you smile.
“Be quiet. Don’t knock it till you try it.”
He just chuckled again. “So, since it’s Friday night Sam and I decided we wanted to do something fun. We invited a bunch of people over for movie night and game night. All of our remaining friends are coming here. Lot’s of snacks, lot’s of alcohol. You in?”
“Uh, I don’t know De.” You hesitate and he frowns.
“I know how Benny and Charlie can get when they drink. I-I, I don’t know.”
“I know you’re shy sweetheart. And that’s okay. But please, it’ll be fun. If you want, you can stick by my side. I promise.”
You pondered over that. “You promise you won’t leave me by myself for long periods of time?”
“I promise.” He held out his pinky and you linked yours with his. He kissed it before pulling away and it made you smile.
“They’ll be here in a couple hours. I’ll see you later?”
“See you later.” You assure him and he smiles before shutting your door.
You knew you sounded a little pathetic, but you were really awkward and shy. The only person you’ve ever opened up to was Dean and that even took some time.
You weren’t as thin as you would’ve liked. You were bullied throughout your entire life over your weight and even your own parents made comments about it.
You looked through your closet, and tried to find something decent to wear. You slid on a pair of jeans and frowned when they fit just right. You used to have a little bit of wiggle room but you must’ve gained more weight without realizing. Still, they looked decent so you chose them.
You were struggling with a shirt to find. You had a few good ones, but you really wanted to impress Dean tonight. You’ve been harboring feelings for him for a while now. Everyone knew how you felt about him except for him.
You loved your friends, but when they drank they tended to slip things out. You really didn’t want your feelings to be spilled tonight. It was one thing if you told him yourself, but if he found out through someone else it would be humiliating.
You found something decent to wear, and you decided to apply a little makeup for once. You only kept some for rare occasions, but you wanted to switch it up. You looked at the clock and saw some time had passed and your friends would be here soon.
As you made your way to the kitchen you instantly smelt Dean’s famous nachos and saw that he ordered pizzas. Beer and liquor were on the counter, and there were a lot of snacks. “Wow, you really went all out tonight De.”
He spun around and flashed you a smile. “I figured I should do something nice.”
“Cas, Benny, Charlie, Jody, Donna, Garth, Claire, Alex, and Eileen. Sam is going to pick her up now.” He says.
“I love Eileen. I’m glad she’s coming.”
“Yeah, hopefully Sam will make his move on her tonight.” He chuckled and you smiled in agreement.
Sam returned with Eileen, and one by one everyone was showing up. Everyone was having a good time just talking, and then you all decided to watch a movie. The movie was honestly lame, and everyone was getting drunker by the minute.
“This movie blows, let’s do something else.” Charlie says slurring her words.
“Oooh, how about truth or dare?” Benny also slurring his words and your heart dropped.
You hated this game. Either you were dared to do something horrible or you had to spill your guts. With your group of drunk friends, it was a lose lose situation.
Everyone, including Sam agreed, and you sunk down into your spot on the sofa. A comforting hand placed itself on your knee and you looked up to see Dean with concerned eyes. “You don’t have to play.”
“I want to open up more. I’ll play.” You say softly and the game begins.
You went around the circle, and even though everyone was wasted nothing too bad happened yet. Until it got to you. “Y/n, truth or dare?” Benny asked you.
“Uhm, truth.” You wince and he grinned.
“Tell us about your worst kiss.”
Everyone laughed, excited to hear the story. Your heart was pounding out of your chest, and you were immediately uncomfortable. “Uhm, I don’t have a story.”
“You have to! Everyone has a terrible kiss.” Sam says.
“Uh, if I was ever kissed maybe.” You stiffen up and look around. Everyone’s mouths were agape in shock. Amusement filled Benny’s eyes, and you immediately felt stupid and embarrassed.
“You’ve never been kissed? How old are you?” Benny teases and you blush.
“I knew you were a little antisocial darling, but phew.” Benny says and you could feel the tears fill your eyes.
“Knock it off guys. Stop being an asshole.” Dean glared at Benny and he playfully threw his hands up.
“I’m going to head to bed. Goodnight guys.” You say before the tears fell and made your way to your room.
“Sweetheart,-” You were already gone but you could hear Dean yelling at Benny.
Tears streamed down your cheeks. You wanted to maybe confess your feelings to Dean tonight. You knew it was a long shot, but now he probably thought you were pathetic.
You changed out of your clothes and buried yourself underneath your covers. You don’t know how much time has passed by but you cried yourself to sleep. You woke up to a dip in your bed, and a hand placing itself on your back.
You jump up and Dean instantly shushes you. “Shhh, it’s just me sweetheart.” He says and you relax.
“What time is it?” You yawn.
“A little after 1. I kicked everyone out. I lectured Benny. You didn’t deserve to be teased like that.”
“It is what it is. I should’ve never played. It’s not like he was wrong.” You sat up and Dean sat next to you.
“He shouldn’t have treated you like that. I don’t care how much he was drinking. He doesn’t know how to control his mouth.” You just shrugged and played with your fingers.
“I think it’s sweet ya know.” He says to you.
“That you’ve never kissed anyone.” You scoff.
“It’s not sweet. It’s so humiliating. I’m in my twenties.”
“So what? I’m guessing you wanted to save it for someone special? Am I right?” He asks.
“That’s part of it. But, no one has ever tried. I’ve never had the opportunity. I wasn’t popular in school. No one ever chased after me. Guys looked the other way when they saw me. I’m just a loser.”
“You’re not a loser. Not at all sweetheart.”
You just shrugged and the tears entered your eyes once more. “Hey..” He cooed gently when he noticed. “C’mere.”
He tugged you into him and you let the tears fall down, he wiped each and every one of them away. “You know, I can think of one guy who is absolutely head over heels for you.”
“Me.” You were shocked.
“Yes. I have been for a long time. You take my breath away.”
You couldn’t help but let your lips curl up shyly, and he loved the redness appearing in your cheeks.
“I really like you too, De.”
He rubbed your cheek with his thumb, and looked at you with so much adoration. “Do you mind if I’m the first?”
He was looking at your lips, and your breath hitched. All you could do was nod, and he moved closer. Hoping to god you knew what to do, you pucker your lips and kissed him back.
He took the lead, and your lips moved together in sync. After a while you both pulled away. You looked up at him shyly, and he was staring at you in adoration. “How was that?”
“Perfect. Everything I could’ve hoped for.”
“Will you be my girl?” He asked you softly and you leaned in, kissing him again. He kissed you back with so much passion, he didn’t need you to answer, he already knew.
Dean Taglist- @agirlwithdemonblood, @akshi8278, @penguinlover0318, @lyarr24, @deanandsamsbitch, @katbratsupernaturalwhore, @flamencodiva, @avanatural.
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for @jactingjoices 1k follower celebration
Day 1 Prompt: I told you so/better together
2.5k. Who The Hell Is Clark Kent? by FallenAngelOfThursday
summary: Set eight months after defeating Chuck and getting Cas back. Dean has been working hard to get his crap together. He's not afraid of much, but when it comes to getting a pair of reading glasses, he's stumped. Nothing a little flirting with his angel can't fix.
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“Forget it, Cas, I’m not going in.”
Castiel sighed. “You have complained all week about how expensive they were, Dean. If you don’t go in there, I’ll-“
“You’ll what?” Dean rose his brows.
Cas turned to him fully in the car seat. They were parked in a loading bay; the only part of the street large enough to fit Baby. The ticket guy could come at any moment, and they didn’t have the time to waste on Dean getting cold feet.
A single brow rose on Cas’ forehead as he stared Dean down.
The bastard loved to watch him squirm.
“Or I will return the cowboy hat I bought as your reward.”
Dean blinked rapidly. He felt the heat rising at the back of his neck, flushing all the way to his cheeks. “You,” he started, unbuckling his seatbelt to face the angel fully. “You got me a cowboy hat?” His voice came out in a low conspiratorial mumble. Was Cas serious right now?
To Dean’s surprise, the angel’s cheeks pinked a little. Cas wasn’t the type to get embarrassed, especially when it came to their bedroom.
“I didn’t buy it for you,” Cas said. He tilted his chin up, shooting Dean a pointed look.
“I ever tell you I love you?” Dean grinned, shaking his head a little in disbelief.
Cas smiled softly. “I enjoy hearing you say it.”
Dean leaned forward, frowning at the building across the street. “Even when I’ll look like a dork?” he grumbled. Cas’ hand settled on the back of his neck and Dean closed his eyes, relaxing into the touch. Cas bent forward and pressed a kiss to his cheek.
“They’re glasses, Dean,” he mumbled in his ear. “The ability to see doesn’t make you a dork. Forcing me to watch the Star Trek movies twice this month alone makes you a dork.”
“Shut up. They’re classics.” Dean blew out a breath. Why was this such a fucking issue? He’d talked it through with his therapist just yesterday. Which reminded him, he should really send the poor dude some flowers or some shit. Is that a normal thing to send someone who’s listened to you bitch about every problem once a week for eight whole months? Did Seb even like flowers? Dean pinched the bridge of his nose and let out a long sigh.
“Dean?” Cas said softly, bringing his other hand to Dean’s cheek, prompting him to meet Cas’ gaze.
Dean’s knees were shaking.
“Nothing’s going to change, Dean. Do you remember what you told me?”
Dean swallowed hard. Yeah, they were just glasses. It wasn’t the glasses themselves – well, not really.
He was getting old. He’d never expected to live half as long, never mind make it to his forties. Then again, he never expected to fall in love with an angel. Or that after twelve whole years of world-ending cockblocking and, admittedly, piss-poor communication, he’d find out Cas had always loved him too. That they could actually have this.
Seb had told Dean he was grieving. At first, it sounded like bullshit. How can you grieve for yourself? It didn’t make any damn sense. But they’d leaned into it for a couple of weeks. Seb had been going hard on the homework these past few months, and it was exhausting. But looking back, Dean could see the difference it’d made. He was grieving: for the time he and Cas had lost. For all the years he’d sacrificed himself – treated himself like he didn’t matter – when there was a chance he could have had everything he ever wanted, if he’d only had the tools to reach for it.
Dean smiled to himself. Seb really spoke his language. He was a good guy. He knew exactly the right metaphors to keep Dean’s head in the game and wasn’t afraid to call him on his bullshit either. Dean didn’t always thank him for it but… it was a process. At least, that’s what all the books said.
“I’m being stupid,” Dean said, trying and failing to fake a smile. He tugged on Cas’ wrist, pulling the angel’s palm toward him so that he could plant a soft kiss there.
Cas looked at him with more patience than Dean had the time to fathom. “Fear isn’t stupid,” the angel murmured. “You’ll still be hot and scary with glasses on.”
Maybe it was the way Cas said it, but Dean choked out a laugh.
“What?” Cas grumbled.
“I’m going to look like an old man,” he said firmly, putting an end to the matter. Still, he felt a little lighter already.
Cas rolled his eyes, gearing up for the same protest he’d had all week. If Dean were honest, most of the time he complained, he’d just wanted to push the angel’s buttons. Cas always found some fun way to shut him up.
Before the love of his whole damn life could bitch him out, Dean pressed a soft kiss to Cas’ lips. It took a while before he’d been comfortable with any kind of PDA, but these days it felt good. Shit, it felt fucking great. The freedom to kiss Cas was one thing, but to do it anytime and anywhere he wanted… there was no other rush like it. Cas didn’t have a single reservation about it. Sam and Eileen hadn’t visited in a while and they suspected it was because of how obnoxious he and Cas were in the privacy of their own home.
Dean couldn’t help the grin that spread across his face and broke the kiss.
“What are you smiling about?” Cas asked, his eyes dazed and sparkling.
Dean shook his head. “Let’s go. If anyone tries to tow Baby, I will murder them. And I do not wanna be the guy wearing glasses in his mugshot.”
Cas only stared in exasperation as Dean got out of the car.
The traffic was light for this time in the evening. The sun was setting beyond, amber light splitting between the city buildings and bathing the damp ground in shimmering light. Dean crossed the road, hand in hand with Cas. He felt like a damn kid right now. Why was he so nervous? The hard part was over. Tests done. Expenses paid. He just had to pick the damn things up and go.
“Mr. Winchester?” the same lady from his appointment last week waved them over from behind the counter.
Dean rolled his shoulders. He dropped Cas’ hand, leaving the angel to sit with a group of old ladies in the waiting area.
“Uh, hey,” Dean said as he approached the desk.
“Right this way,” she smiled. Dean rolled his eyes, shooting a pained look in Cas’ direction. The angel shot him a thumbs up. His tongue peaked through his smile, and his eyes shone with sincerity.
Dean’s heart squeezed at the sight.
He could do this. He’d be a good boy and get his Clark Kent on. And later…
“Take a seat,” the lady said, gesturing to a small table around the corner.
Dean sat. He waited. He picked at a stray thread on the lining of his jeans, and he waited some more. He was growing impatient by the time the lady returned and dropped into the seat opposite. She sat two cases in front of him and Dean frowned.
“Uh, no offence or anythin’ but… I paid out my ass for one pair. I don’t need-“
The lady waved her hand dismissively, cutting him off. “These are your sunglasses,” she said, sliding one of the boxes toward Dean.
He stared blankly at the silver box.
“Your partner saw you checking them out,” the lady smiled pointedly. “He came in and paid for them later that afternoon.”
Dean opened the box, his heart swelling in his chest. He pulled out the pair of sunglasses, turning them over in his hands. They were awesome. Last week, he’d only wanted this pair and decided his eyesight could go to hell. They’d look so good in the Impala.
“Try ‘em on,” the lady said. Dean glanced down to her nametag, squinting as he read Sarah. Sarah rolled her eyes. “You’ll have an easier time reading with your glasses on, Mr. Winchester.”
“It’s Dean,” he corrected, placing the sunglasses on over his nose. Oh shit, he could see. Sure, he must look dumb wearing sunglasses indoors, but-
Sarah held out a mirror and Dean grinned at his reflection.
“These ain’t so bad.”
“Mm,” Sarah agreed. “Your partner knows you well.”
Dean smiled wider. “Sure does.” He placed them back in the box, already thinking of ways he could pay Cas back later.
“Okay, now try these on,” she said, pushing the second box toward him. “If they don’t fit, we can adjust them. No charge.”
Dean gulped as he opened the box. He picked up the frames with gentle fingers. Here goes nothin’.
“It’ll be a new beginning,” Sarah said, watching him with a little too much amusement. Dean shot her a glare, but he put the frames on all the same.
He blinked at his reflection. He’d forgotten how many freckles dotted his nose and cheeks. There were a couple of visible scars here and there from years of hunting but… not bad. He expected to feel a million years old, but now that it came to it, it was no big deal.
“New beginning, huh?” Dean joked. “Clark Kent don’t got shit on me,” He looked over the mirror at the optician to find her staring blankly at him.
“Who the hell is Clark Kent?”
Whatever, Dean thought. Cas would have got the joke.
The glasses did need a little tightening, so Dean was left in his seat for a little while longer. He tried to focus on later, on this supposed cowboy hat Cas had waiting for him at home. Where the hell had he even bought it anyway?
He drummed his fingers on the table, biting his lip. This was his life now, he thought. He wore glasses for driving and TV. He saw a therapist. He had a hot angel boyfriend. They had a Nephilim kid. Dean looked in the mirror again, studying his slightly grown out hair, the thin lines in the corners of his eyes.
Right now, he wouldn’t change a damn thing. He thought of Seb’s words in their last session. Something about how the life ahead of him is more important than the life behind him. It seemed like a dumb cliché at the time, but… maybe it was true. For the first time in his life, Dean was content. Happy. He was making plans. He wasn’t drinking. He was waking up every morning next to his gorgeous best friend, limbs tangled, and cheeks flushed.
For the first time, he was looking forward to whatever the hell tomorrow might bring.
Sarah returned with his frames and Dean tried them on. They fit perfectly. He looked like a dork, but he’d do a lot worse to get his angel into bed with a cowboy hat on.
Dean made his way to the waiting room and found Cas nodding along seriously with a bunch of gossipy old ladies.
“Uh, mind if I steal you, partner?” Dean winked.
Cas’ eyes widened. His mouth opened and closed but no sound came out.
God damn it, he knew he looked stupid. “Told you so,” Dean grumbled, pulling Cas to his feet. “I look like an idiot. Cas waved at the old ladies as Dean dragged him from the opticians.
“I can’t believe you paid for the sunglasses,” Dean said, pulling the dorky frames off his face.
“Leave them on,” Cas said, his voice low and gravelly.
Dean paused half-way to the car. “What?”
Castiel gently took the glasses from Dean’s hand and placed them back on his face. His breath caught in his throat.
“Uh, you’re kinda staring pretty hard there, buddy,” Dean noted, confused.
Cas blinked. Before Dean could form another thought, Cas’ mouth was on his. Dean wrapped his arms around Cas’ waist, returning the kiss until a car stopped behind them and honked the horn, and they were forced to move out of the way.
“Wow there, sweetheart,” Dean panted. “The hell’s that for? Not complainin’, but-“
“Get in the car, Dean,” Cas demanded.
Well, okay then.
Dean said nothing as Cas pulled out his phone, setting a route for their next destination. He didn’t say where and Dean didn’t ask. Honestly, he didn’t have a damn clue what was goin’ on.
A few minutes later, they pulled up at a lake. The place was empty; the last dregs of sunlight bathing the water in tones of fuchsia and gold. Cas said nothing as he got out of the car. Frowning, Dean followed.
“Nice spot,” Dean said. And it was. He wondered how Cas had known about it. “What’re we here for?”
Castiel turned his attention from the lake, his hazy eyes fixed on Dean. He stepped toward Dean, pushing him back onto the hood of the Impala.
Dean scooted on top, wrapping his legs around the back of Cas’ own to pull him closer. “You bring me to a make-out spot, sweetheart?”
Cas crushed his lips to Dean’s without warning, kissing him fast and deep and leaving him totally breathless.
“You’re beautiful,” Cas murmured, his lips not quite parted from Dean’s. “All of you. You’re beautiful.”
Dean felt like the air was knocked from his lungs. He pushed himself further back onto the hood, pulling Cas with him. He planted gentle kisses on his angel’s cheeks, his eyelids, his nose, his mouth. For eight months, they’d been making up for lost time, but Dean knew he’d never grow tired of the weight of Castiel above him; the taste of his skin or the feel of his lips. He’d never get enough of the tiny hitch of breath each time Dean’s lips found Cas’ neck.
“This your way of tellin’ me I got specs-appeal?”
“Stop. Talking.” Cas growled.
“I love you so damn much,” Dean whispered against Cas’ skin, bathed in the dying light of the day.
Castiel had fallen from grace in every way imaginable for Dean, until there was hardly a spark of it left in his veins. From the moment he’d gripped Dean tight and raised him from perdition, Dean had been falling ever since. Dean fell and fell, and sure, half the time he’d been stumbling blindly, drunkenly, trying to claw his way back up with broken nails and bleeding fingertips, but his descent into his love for the angel was never ending.
Somewhere along the way, he’d accepted that. He’d enjoyed it in the quiet moments; a small smile to himself alone in his room, a twinkle in his eye seeing the angel at the breakfast table, a photograph held to his heart before every hunt. For years his love had been a shameful, secret thing.
Eventually, finally, he’d embraced it. And now that he had, he discovered that those impossible celestial hands that had once built him from the ground up were right there to steady him. Through every kiss, every hunt, every time they almost lost each other again and again, every sleepless night and every long drive with Cas’ hand resting atop his on the gearstick. He felt only pride for his love for Cas. There were no more secrets, only truth.
Dean was still falling, but Cas – the angel had never flown higher.
“I love you too, Dean.”
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